Transaction
by charmed7293
Summary: Jack has a lot of customers. They usually come and go, but Pitch always comes back for more. While Jack can't help feeling attracted to him, there's something dark and dangerous about the way Pitch returns that affection. Even so, the pay is too good to pass up. (Based on prompts from the BlackIce 30 Day Smut Challenge.)
1. Sensual Foreplay

Over on Tumblr, May is BlackIce Smut Month! Everyday has a different prompt and I'm going to do my best to fit as many as I can into the overarching plot I have planned. Since May is a very busy month for me, I probably won't finish within it and a single smut scene may be broken up over several days, as well as each day being rather short. To make up for that, the whole thing is technically Day 16 (Brothel) and Day 23 (On the Job).

This is for Day 1: Sensual Foreplay

* * *

"Lie on your left side and draw your right leg up to your chest."

Jack did as he was told without hesitation, spreading out on the crisp sheets. His clients didn't pay him to question them and Pitch was one of his largest sources of income. It wouldn't do to lose his business.

He felt the bed dip as Pitch settled behind him, but he kept his eyes closed, as per previous instruction. Hot breath gusted against his shoulder as two lubed-up fingers pressed against his hole. Jack gasped and canted his hips slightly at their cool touch. Pitch took his time circling and massaging before sliding a finger inside. That warmed it up quickly enough.

Pitch's gentleness continued as he moved the single digit in and out, waiting until he was sure Jack was ready before adding a second. There was really no need for such care—Jack had gotten used to being penetrated mere minutes after entering a client's room by people too inexperienced to even know what foreplay was—but it was certainly appreciated. He sighed in pleasure and let the muscles in his face go slack.

Pitch's breath quickened as he stretched Jack, coming in faster puffs against his back. He liked watching Jack's reactions to his ministrations, so Jack tilted his face up, offering Pitch his neck, and pushed back on his fingers, as if asking for more.

Pitch growled softly in satisfaction and thrust his fingers harder. He leaned his face down to Jack's neck, kissing and sucking gently, careful not to violate Jack's rule of no marking.

The addition of a third finger really made him feel the stretch, drawing out a moan as well; the only sound in the room. Pitch's silence was a surprising, though welcome, change from his usual running mouth. Jack wondered if something was going on in other areas of Pitch's life, causing him to cease his endless stream of words. It would also explain why Pitch had requested him for twice as long as he usually did. His normal hour was already longer than most of Jack's other clients, so Jack couldn't image what he could possibly want to do. It had already been a half hour and, until he told him to close his eyes and get on the bed, Pitch had only stared at him, making Jack squirm under the attention. He was used to eyes sliding over him and looking at him only as an object to be used. Someone staring at him as if he was a work of art to be admired and appreciated was unnerving to say the least, though Pitch still didn't look at him as another human being. Jack was still something he had bought, something to be consumed.

Pitch twisted his wrist and his fingers struck Jack's prostate on their next thrust, making him cry out. This was why Jack didn't mind dedicating so much of his time to Pitch. He was far from inexperienced and derived just as much pleasure from Jack's pleasure as _Jack_ did.

Pitch kept up his assault on Jack's prostate, though he drew his fingers out less and less with each thrust. Eventually, they were just rocking against his prostate, supplying constant stimulation. Jack moaned hoarsely and held back from squirming, not wanting Pitch to stop. Pitch pressed his face against Jack's neck as he breathed heavily and Jack could feel how hard he was from where he was pressed against the back of his leg.

Pitch spread his fingers, the tips still brushing against Jack's prostate, and withdrew them slowly. Finally satisfied with the thorough stretching he had given Jack, Pitch sat up.

"Lie on your back now."


	2. Vanilla

Day 2 is Vanilla and missionary position is as vanilla as I'm going to get. ahahah Also, ending smut scenes is difficult and awkward.

* * *

Jack slowly rolled onto his back, careful not to hit Pitch with his left leg as he moved it to his other side. He watched as Pitch rolled on a condom, another one of Jack's rules. He'd turned away countless potential customers because they complained about that rule, but there were always other desperate, greedy people who would accept his services with that condition, so he didn't need to bother himself with those who wouldn't.

Pitch gripped him under the knees to lift and spread his legs. Jack hooked them over Pitch's hips as he guided them there.

Typically, this was when Jack would distance his mind from the current situation and think about other things: grocery shopping, laundry day, when those damned medical bills needed to be paid. It's not that he felt violated, but he didn't exactly enjoy having sex with people he wasn't attracted to. With Pitch, it was different. Jack didn't feel the need to detach himself from the moment. He didn't necessarily find Pitch attractive, though he was far more appealing than many other regular clients, and it didn't have anything to do with how he looked.

It had more to do with the way he treated Jack, almost as another human. The way Pitch held him and the things he said were like those directed at a lover. Pitch even used his name, instead of whomever the other clients had hired him to help them forget. Jack could pretend those caring actions were actually meant for him, just for him.

That's why, as Pitch pushed into him, Jack didn't allow his mind to wander, but focused on what was happening. It was slow, gradual, and Pitch had time to slip his arms behind Jack's shoulders and around his waist to pull him close before his hips met Jack's ass. Jack gave a satisfied hum and even dared to put his arms around Pitch in return, though he started with just his hands on Pitch's shoulders, gripping tightly.

Pitch started moving and Jack arched his back at the feeling. It was so gentle, so unlike the unrelenting pounding he usually got. Minutes passed with Jack's soft sighs and the creaking of the bed as the only sounds, but it wouldn't be long until Pitch started talking.

As if on cue, Pitch whispered his name.

"Jack . . ."

It was just a breath in Jack's ear, but it meant more to him than anything else people had said to him.

"This gets better every time I have you. I could never tire of you, Jack."

Jack shuddered in Pitch's embrace and slid his arms all the way around Pitch's shoulders. This wasn't the most conventional . . . _business_ relationship and probably wasn't the healthiest either—obsession was dangerous, especially in his line of work—but Jack liked someone taking care of him for a change. He liked being able to relax and not worry about the client being dissatisfied because Pitch was satisfied as long as his mouth was running.

"If only I could keep you all to myself, but I can't . . . I would like to say that's because no one should be deprived of you, but that's so far from the truth. I would really rather keep you away from everyone else, just for me. But sadly I have other responsibilities. I always wonder . . . how much would it cost to have you waiting for me every day?"

Jack didn't bother answering, only moaning as Pitch struck his prostate. It's not as if Pitch was expecting or waiting for a response, anyway.

"Hmmm, you like that? Right there, Jack?"

Pitch kept himself angled so he continually hit Jack's prostate, wringing more moans and whimpers form him.

"I love the sounds you make, Jack. And you make them just for me, only for me. You may fake them for other people, but I'm the only one who can truly _make_ you react like that."

Jack still didn't say anything, but it was undoubtedly true. Most clients didn't give a thought to his pleasure, yet still expected him to react as if they were some kind of sex god. He never had to pretend for Pitch.

Pitch pulled back slightly, trailing his tongue over Jack's neck and then down his windpipe, only stopping when he reached Jack's collar bone. His lips pressed firmly against the dip in the center before sucking harshly.

"Yes, you're doing this all for me and you know why? Because I'm doing this all for _you_."

Jack came suddenly with a muffled shout, throwing his head back and digging his nails into Pitch's skin. He only gripped tighter as Pitch's thrusts sped up.

"Jack!" Pitch grunted as he came. His nails dug into Jack's skin, breaking it and drawing blood, only returning the favor Jack originally gave.

Pitch pulled out and collapsed to Jack's side. He threw an arm over Jack's waist, just lying there, catching his breath.

Jack allowed it, for now.


	3. Shower Sex

Day 3 is Shower Sex. There's one line in here that makes me really embarrassed, so try to guess what it is. ahaha

* * *

"You still have an hour left," Jack said, speaking for the first time since he entered the room. They had been lying there for quite some time now and he was starting to get bored.

"I know," Pitch said, but he didn't move.

Several long minutes passed and Jack felt his eyes beginning to drift shut. He really shouldn't fall asleep on the job, but it was hard when he was bored out of his mind and inexplicably comfortable around Pitch.

"Shower with me?" Pitch finally said, snapping him awake.

Normally, Jack would never consider such a thing. It was far too intimate for the distance he liked to keep from his clients, but a lot of the things Pitch did crossed that distance as if it were mere millimeters. There was no point in upholding the pretense that there was no intimacy in their interactions.

"Sure," Jack said. Besides, depending on what happened in the shower, Jack could charge more money. He had a base price that covered thirty minutes of his time and sex, but addition time and acts cost extra, especially depending on the person (as if he was going to willingly get on his knees or do anything else for a sweaty, skeevy-looking creep who smelled like they hadn't bathed in at least a week).

Also, he was still bored and at least this would be interesting.

He waited for Pitch to move his arm before rolling off the bed, landing on his feet and stretching his arms over his head. He froze as Pitch's hand touched his side, just under his ribs, and trailed down to the curve of his ass, digging fingers into his cheek possessively. He turned his head to look over his shoulder and glare half-heartedly at Pitch.

"You shouldn't tempt me," Pitch said, smirking.

Jack let out a breath of laughter and shook his head. He headed for the bathroom, sensing Pitch getting out of bed and following him.

While he waited for Pitch to start the water and adjust the temperature, Jack glanced at himself in the mirror over the sink. His eyes were immediately drawn to a discoloration in the center of his upper chest. With a soft gasp, he stepped closer and rubbed his fingers over the mark, clearly a hickey.

Pitch came up to stand behind him and Jack glared at his reflection in the mirror.

"No marking," he said sternly, frowning. "You know that."

"Sorry," Pitch said with a smirk, not sounding the least bit so.

Jack just sighed. At least it would be easy to hide.

Pitch swiped his fingers over the hickey before grabbing Jack's hand and pulling him into the shower. Under the stream of water, Jack forgot all about the mark and being angry at Pitch. It was the perfect temperature and the powerful jets massaged away his stress. It was far better than his usual shower, which was typically a five-minute rinse down, sometimes between customers if he was lucky enough to find one who was willing to pay for a hotel room.

He let Pitch wash his hair, an act strangely more intimate than the sex they just had. Pitch refused to allow him return the favor, but Jack was fine with letting him do all the work for both of them. After he rinsed the shampoo from his hair, Pitch pushed his soaking bangs away from his face.

"Can I do something to you?"

"Do what exactly?" Jack asked warily. Pitch often requested to do some rather _different_ things and though Jack found them pleasurable more often than not they were still pretty weird.

"Oral," Pitch said.

"Sure." Jack couldn't help but feel somewhat disappointed, though he wasn't sure if it was because he wouldn't be able to charge extra when Pitch was the one giving _him_ pleasure or because it wouldn't be something new. The latter also made him wonder why Pitch had asked as if this was something new he wanted to try. Pitch had given him blowjobs plenty of times before.

Pitch's smirk was the only warning he got before he was suddenly turned and pressed face first into the wall. He was confused until Pitch knelt behind him, cupping his ass with his hands and spreading his cheeks with his thumbs. Pitch hadn't specified which _part_ of his body he was going to perform oral on.

Jack didn't have any more time to think about Pitch's trick, as his tongue was suddenly at his entrance, circling around and pressing the tip inside. Jack gasped, caught between wanting to squirm away and push back against Pitch's face at the same time. No one had ever done this to him before and it had never been requested of him either, so this was all very new and he had no idea what to expect. Pitch seemed to know what he was doing, if how good it felt was any indication.

Jack muffled his whimpers as best he could into the tiles and his fingers scrabbled for purchase against their slippery surface. He desperately tried to uncurl his toes, the smoothness of the ceramic floor combined with his fidgeting making him nervous. He wasn't too interested in falling.

Pitch's nails dug into his skin, anchoring him. Pitch wouldn't let him fall. Jack didn't need to worry. He could just let go and enjoy himself. A more audible whimper escaped his throat.

"That's it, Jack," Pitch said, pulling away for a moment. "Let me hear you."

As he moved back in, Pitch's left hand pulled his ass cheek further apart and his right hand moved around to stroke Jack. Jack threw his head back, letting his cries echo off the ceiling. He had just come not even fifteen minutes ago, but he was already so close.

Pitch hummed, sending vibrations through his tongue and directly into Jack's ass. Jack choked on his moan and desperately searched for something to grasp onto. One hand found the soap dish and the other clutched at his face before settling in a grip on his hair. He arched his back as far as he dared to without being afraid of falling over.

"Pi-p-please—" Jack caught himself before he called out Pitch's name. That was not the kind of impression he wanted to give. He couldn't let his guard down, but that was rather hard considering it was already shattered and Pitch was currently rimming his asshole raw.

Biting by another cry that wanted to turn into Pitch's name, Jack came. Panting heavily, he leaned forward until his forehead was pressed against the cool tiles. Pitch stood up and rested his own forehead on Jack's shoulder.

Once he felt he was able, Jack turned to face Pitch. "Is there anything you want?"

"No, that was enough," Pitch said with a strange smile. Confused, Jack just nodded and let them continue with the shower, but the warm water couldn't ease away his thoughts this time. But this was all something he could think about later, when he was home and away from Pitch.

They got out of the shower and Jack put his clothes back on as soon as he was dry enough. He was eager to just leave. Well, first get his money, and then leave.

"Are you sure you can't say?" Pitch asked. It was the same question he asked every time and Jack gave the same answer.

"I need to go home."

"Fine then." As always, Pitch sounded so disappointed. "Here's your money."

He held out an envelope. As Jack reached to take it, Pitch pulled it away. Jack's eyes shot to his face, only to see a gentle smile.

"First, a kiss."

Jack's heart jolted in his chest. Pitch had never asked for a kiss before. No one had ever asked for a kiss before. In fact, Jack couldn't recall a time when he had even kissed _anybody_.

"What?"

"A kiss, Jack."

Pitch stepped forward and wrapped an arm around Jack's waist, pulling him close and pressing his lips against his. Eyes widening in shock, Jack simply stood there. He didn't know how to react. He supposed it felt nice, but it was so intimate. He wasn't used to this level of affection.

But then it was over just as soon as it started and Pitch stepped back. Jack remembered to breathe again.

"Here," Pitch said smugly, holding out the envelope again. Jack took it with shaking hands and hurried out the door.

* * *

I'm sorry to spread out a single scene over three days, but it had to be done due to my own time constraints and the nature of the prompts. How do you guys like the story so far? The next few chapters will have some situations involving prostitution, which I have no real life experience with, so I would appreciate some feedback on how I'm doing so far.


	4. Interlude

This is rather short and doesn't follow any of the smut challenge prompts, but it does explain some background things. It's also late because I was away the past couple of days. I'm still busy with school, so hopefully I can reply to reviews soon! Always open to feedback!

* * *

Jack stopped as he passed the convenience store a block away from his building. He considered only for a second before going inside and heading straight for the freezer cases. Grabbing two cartons of ice cream, he tried to discreetly pull out one of the smaller bills from the envelope to pay.

A bounce now in his step, he quickly covered the rest of the distance to his building. He was too impatient to wait for the elevator, so he sprinted up the stairs instead. A little out of breath, he stopped on the fourth floor to knock on the door of apartment 407. He could hear children laughing and some kind of evening talk show from within. The sounds only amplified as the door opened.

"There you are," Tatiana said, relief clear on her face. "You're quite a bit late. I was started to get worried."

Jack smiled at his neighbor, touched, though not surprised, by her concern. "Sorry. I had to work a little longer, but it was worth it."

He held up one of the plastic bags. The condensation from the carton made the bag stick to it, clearly revealing its contents.

Tatiana's eyes lit up and she gratefully took the bag from him. "You're too much, you know that?"

"It's nothing, really!" And it wasn't. Jack wanted to give her so much more than just ice cream, but he had long since learned she wouldn't accept it.

"Jaaaaaaaaaaack!"

Jack's smile grew brighter and he bent down to catch the flying streak of brown hair that had just launched itself at him. Emma shrieked in delight as he swung her up over his head.

"Did you have fun today?" he asked as he lowered his sister to the floor.

"Yeah! After school we went to the park and then we came here for dinner and then we played. Tia got new dolls!"

"Did she now? Where is she?" Jack glanced at Tatiana questioningly. The absence of her daughter was strange. She usually ran to greet Jack just as fast as his own sister did.

"Emma, you can't just throw them!" It seemed like he thought too soon. Tia came out of her room, tenderly holding a doll and gently untangling its slightly snarled hair.

"But Jack's here!" Emma insisted.

"You still shouldn't do it," Tia said and stuck her tongue out.

Emma stuck hers out in return and took a breath to retort.

"Ooooookay," Jack cut her off, physically covering her mouth for good measure. "That's enough of that. Time to go home."

"But I want to keep playing," Emma whined.

"Me, too! Don't make her go." Tia clung to Emma, their earlier disagreement completely forgotten.

"I have a surprise for you," Jack said, holding the bag behind his back, "but only if you come home now . . ."

"Fiiiiiine," Emma said with a huff, sounding reluctant, but Jack noticed the way she tried to peek at the bag as she walked through the doorway.

"Thank you, Miss Tatiana! Bye, Tia!"

"Thanks, Tatiana," Jack said, waving as he let Emma pull him toward the stairwell.

"No problem, Jack. I'll see you later." Tatiana smiled one last time before she shut the door.

"So what's the surprise?" Emma asked, hopping up the stairs. She stopped suddenly on the landing. "It better not be a trick!"

"It's not."

"Are you lying?"

"I'm not!" Jack laughed at the suspicious look he got—though it also pained him, looking so alike their mother's as it did. "Believe me?"

Emma looked down at him from the top of the flight. "Of course."

"Good. Are you read for some ice cream?"

"Ice cream! YES!"

Emma ran to their door and bounced impatiently as Jack unlocked it. He had to hold himself back from doing to the same. It was so rare they got a treat like this, but that made these moments all the more special.

* * *

Later on that night, while Emma was sound asleep in her bed and their ice cream dishes soaked in the sink, Jack took the envelope out of his pocket and carefully counted the money. _His_ money.

He dug through one of his drawers, taking out a fireproof box. He laid out all the money in designated piles: groceries, clothes, school supplies, rent, hospital bills, emergency money.

He divided that day's earning into those piles, able to put a bit extra into groceries and emergency money. Thanks to Pitch. Jack sighed and shook his head to clear it of those thoughts. Money was money and he needed it. He couldn't afford to be picky about who or where it came from. Yes, he got a bit more this week, but that was thanks to his own skill and appeal, not Pitch's generosity. Pitch paid for what he got, so Jack shouldn't hold him in high regard.

With a huff, he stuffed all the money back into the box and chose a new hiding spot for it. Since he had technically already showered, he decided to forgo that for the night. Setting his alarm, he changed into a T-shirt and a pair of boxers and crawled under the covers. He was asleep before his head hit the pillow.


	5. Toys

Day 4 is Toys. This one ends rather abruptly, but the next part picks back up right where this leaves off. It's a bit awkward, but, again, had to be done to fit within the prompts and my own time constraints.

* * *

Jack leaned back against the brick of the alley wall, letting his shirt ride up a bit and expose a strip of pale stomach. As anticipated, it immediately drew the gaze of the young man with whom he was talking. His eyes wandered down and Jack shifted his legs, quite nicely emphasizing his crotch and further catching the man's attention.

Things were going exactly as planned. Jack had snared the man's interest the moment he saw him, but he still had to ensure he didn't lose it. There was a near endless selection in the red light district of a city this big.

Jack smiled invitingly and the man leaned closer, propping his arm on the wall beside Jack's head.

"So . . . how much for an hour?"

There it was.

"That depends . . . what do you have in mind for that hour."

The man didn't hesitate in responding. "A blow job and then sex. You top."

Now _that_ was interesting. Jack usually bottomed by default and he didn't recall anyone specifically requesting he do otherwise. That combined with the fact the man was actually rather attractive made Jack consider not charging as much extra as he usually did for the blow job—though at this point he almost wondered if he would be the one giving it, anyway.

"Jack."

Jack's brow furrowed in confusion at hearing that voice. He looked down the alley, in the opposite direction his potential customer had come from. Pitch stood just a few feet away. Jack blinked at him, not knowing what to make of his being there.

"Who are you, his pimp?" the man asked, almost defensively.

"Hardly." Pitch spared him a bored glance before focusing back on Jack. "I require your services."

"Hey! Back off! I got here first."

"I understand this is such short notice and you seem to be . . . otherwise occupied," Pitch continued, speaking directly to Jack and ignoring the man, "but I will pay you double my usual amount."

Jack's eyes widened and his lips parted in surprise. He had no idea what was making Pitch so desperate lately, but he wasn't going to question it if it came with results like this.

"Okay." He turned to the man. "Sorry, gotta take this. Hope to see you around."

Jack winked at him even as Pitch glared and grabbed his wrist to pull him away, leaving the man to stare longingly after them.

As they exited the alley, Jack pulled his arm away from Pitch. He didn't need anyone seeing a client dragging him around.

"What's with the jealousy?" he asked, only half-jokingly. "I _do_ sleep with other people. It's kinda my _job_, you know."

"Yes, I know," Pitch responded tersely, very much sounding as if he wasn't pleased with that fact.

"You don't own me," Jack said firmly. Pitch only gave him a look that said he would prefer otherwise.

Jack really should have gotten out of there as fast as he could. It was _dangerous_. He didn't know why he was continuing to follow Pitch.

Well, actually he did. The money. He needed that money. He'd already weighed the potential consequences of Pitch's apparent obsession with him against not getting his money countless times. Servicing Pitch was as close as he was going to get to a steady, reasonably-sized income. Jack tried unsuccessfully to convince himself that the money was the only reason, that it had nothing to do with the way Pitch treated him during the act . . .

Besides, it's not as if Pitch had done anything too concerning yet. Words didn't mean anything until actions followed to support them. Jack knew that all too well.

So he followed Pitch to a nice looking hotel where they went directly to an elevator and up to the sixth floor. Pitch's room was near the elevator doors and he ushered Jack inside. Since Pitch clearly had this room before he approached him, Jack wondered what he would have done if he refused his proposition. Probably just offered more money. Maybe he should have turned Pitch down and waited for him to triple his offer.

Jack stood in the center of the room as waited for Pitch to finish rummaging around in his briefcase. Pitch liked a variety of things and never did the same one twice in a row, so Jack never knew how he wanted to begin.

Pitch finally turned around, concealing something in his palm. "I forgot to mention that your double payment _will_ come with one small condition."

"If I don't agree—"

"Then we will just proceed as usual, with the regular price."

"Fine by me."

"The condition is: you wear this." Pitch held out his hand, revealing a slightly-studded circle of silicon.

"A cock ring," Jack said, reaching out and taking said ring from Pitch, who circled around behind him.

"Yes," Pitch said as he placed his hands on the protrusions of Jack's hipbones. "I assume you know what it's for? When wearing it, you won't be able to come until it's taken off, until _I_ decide to take it off."

Jack swallowed, surprised at how dry his mouth suddenly was. As much as Pitch's obsession with him was dangerous, it also guaranteed his safety in a way, at least when they had sex. Pitch wouldn't harm him because he wanted to ensure he would come back receptive and unafraid. That meant he was free to relax (a little bit) and actually enjoy their activities. And this was definitely something he wanted to enjoy.

"Do you agree to this?"

"Yes." There wasn't much reason _not_ to agree.

"Good," Pitch purred, but his smile said the opposite. "Strip and sit on the bed."

Jack did so, methodically removing his clothes. He lowered himself onto the bed and slightly spread his legs. He wasn't exactly sure how a cock ring worked or was used, but its name and design pointed toward it going on his cock.

Sure enough, Pitch stepped up to him and lightly stroked his already hardening cock before slipping the lubed ring around it, sliding it down until it was snugly around the base. As Pitch continued to stroke him, the pressure increased and Jack felt how this could easily hold back his orgasm.

"Get on your hands and knees in the middle of the bed."

Jack slowly turned around and crawled farther onto the bed, trying to ignore the way his cock throbbed much more noticeably at the order. He lowered himself down onto his elbows and made sure his legs were adequately spread. Pitch's lubed-up fingers pressed against his hole, one slipping inside. Pitch's other hand, instead of roaming his back or legs like it normally did, reached around to stroke his cock. As he did, he added a second finger and began scissoring them.

Jack just let the sensations roll over him. Pitch's fingers and hand were painfully familiar, but the pressure that increased as he got harder wasn't. He wouldn't describe it as uncomfortable, but it was certainly strange.

He whimpered into the blanket as Pitch's fingers struck his prostate, causing his pleasure and the pressure to spike. He expected Pitch to continue, but he changed the angle of his fingers, only switching back to his prostate every few thrusts. Pitch didn't often tease, preferring to get straight to the point, but when he did, it felt like torture. Not being able to come made it so much worse.

The next time Pitch hit his prostate, he ran his thumb over the head of Jack's cock, which definitely would have made him come if he were able. Jack cried out in pleasure and frustration and Pitch laughed rather darkly.

He leaned down and pressed his chest to Jack's back, fitting their bodies together. Putting his mouth directly next to Jack's ear, he said, "It's frustrating, not getting what you want, isn't it?"


	6. Orgasm Denial

For this one I skipped head to Day 22, Orgasm Denial. Though it's more like orgasm delay, because even I'm not that cruel.

* * *

Pitch quickly sat back up and busied himself with putting on a condom, leaving Jack to think about what he just said. It certainly didn't do much to reassure Jack of his previous doubts. The words themselves seemed harmless enough, but the way they had been said, especially coupled with that laugh, sent chills down Jack's spine.

He wasn't afforded more time to dwell on that as Pitch pushed into him. Jack switched his focus to relaxing and allowing Pitch to sink into him with as little resistance as possible. Pitch gripped his hips and pulled him back the last few inches. Jack gasped at the fullness as he felt Pitch's hips against his ass.

Above him, Pitch breathed heavily, but otherwise remained silent. Jack didn't take that as a good sign. Pitch pulled out almost all the way before snapping back in, setting a rather brutal pace and drawing Jack into his rhythm with the hold on his hips. Every thrust in forced a sharp moan from Jack's lips. He felt like Pitch was tossing him around, jerking him back as thrusts forward pressed his face into the mattress.

Pitch still did not talk. The only sound he made was a grunt as he came, buried deep inside Jack and gripping his hips hard enough to bruise. Pitch's release reminded Jack of the need for his own. He wondered at his fate, seeing as Pitch usually made sure Jack came before coming himself. He whined in distress.

Pitch laughed, only slightly less sinister than before. "Do you want to come, Jack?"

Jack squeezed his eyes shit and frantically nodded his head.

"I can't hear you . . ."

Jack swallowed to stop himself from whining again. "Yes."

"'Yes' what?"

Jack was silent for several moments, unable to bring himself to say it.

"Maybe I should leave you like this—"

"No!" Jack said quickly. "Please. Please, make me come, please."

"That's it, Jack," Pitch said, gently rubbing his back. "But keep in mind that I'm not just making you come. I'm _letting_ you come."

Jack shivered as Pitch's hands slid to wrap around his length. Giving it several strokes, he made Jack squirm in discomfort at his own hardness. Pitch's fingers dipped down to his base and traced along the edge of the cock ring. They circled it and gently pulled it off, careful not to brush any other part of Jack's cock so he didn't come before Pitch wanted.

Jack shifted, desperate for any kind of contact, or relief, but Pitch only chuckled behind him.

"So close, are we?" he asked.

Jack felt like sobbing, but he didn't want to give Pitch the satisfaction. Then Pitch wrapped his hand around his cock and Jack came so suddenly he wasn't sure his gasp was one of surprise or pleasure or relief, though it was probably some twisted mix of the three.

Pitch continued stroking him through his orgasm and only stopped when Jack finally let out a sob, too sensitive to stand the contact. He slowly pulled out and helped Jack lay down on his side. Still panting heavily, Jack relaxed and enjoyed the boneless feeling pervading his body.

His breath hitched as Pitch's chest pressed against his back and his arms slipped around his waist.

"Is this okay?" Pitch asked.

"Yeah, I'm just not used to stuff like this."

"You could be . . ."

Jack didn't bother responding. Pitch already knew what his answer would be anyway. Jack only let himself enjoy their position for a few minutes longer. It did feel nice, but there was no point in playing pretending or sending a message he didn't want to send. Besides, he still had work to do.

Jack let Pitch's arm slide from his waist as he slowly sat up and moved to the edge of the bed. Glancing at the clock, he saw there were still fifteen minutes left in Pitch's hour.

"What do you want me to do for the time remaining?" Jack asked.

"Come back like you were before."

Jack looked over his shoulder at Pitch, who was gazing up at him expectantly, arm lifted in invitation. Jack swallowed and considered. He could refuse to do something if it made him uncomfortable, but being held by Pitch didn't exactly make him uncomfortable. It made him feel nice, actually, like he was wanted and cared for; however, _that_ was what made him uncomfortable. Not the action itself, but how it made him feel. He shouldn't feel this attached to a customer, especially one who was already so attached to him, not matter how well paying they were.

Yet there was really nothing he could do about it. Pitch provided him with the one thing he needed and Jack really couldn't afford to lose that. He hated how everything in his life revolved around money, even influencing choices that should have been his own to make, based on nothing besides his own desire.

With a sigh, he lay back down and let Pitch wrap his arm around his waist again. Pitch pulled him close and tucked Jack's head under his chin. He sighed, though it was one of contentment as opposed to Jack's one of resignment.

Jack stared at the clock on the bedside table, counting down the minutes until he could leave.


	7. Size Difference

Day 6 is Size Difference and here's my disgustingly short excuse for that. It's more build-up for Day 7 (I'm sure you can guess what that is), but I wish I did better since this is such a _huge_ kink for me.

* * *

Tuesdays were always slow. Even _Monday_ was busier, with people seeking relief from the beginning of the week, or Wednesday, since people apparently didn't understand it was called "Hump Day" because it was the middle of the week.

Heaving a sigh, Jack pushed off the wall of the deserted alley. If there was no one around, he might as well go home and take Emma off Tatiana's hands early.

"Where do you think you're going?"

But there he was, Jack's reason for bothering to come out on Tuesday at all. He turned to watch as Pitch strode toward him.

"I figured you weren't coming," Jack said.

"Oh, I'll be coming," Pitch said, smirking. Jack rolled his eyes at the not-so-subtle innuendo. "If I can stop you from running away, that is. Maybe I'll have to tie you up."

Pitch stopped in front of Jack and looked down at him appraisingly. Jack was going to get a crick in his neck with how far up he had to tilt his head to meet Pitch's eyes. They hardly ever stood next to each other this close, so Jack never realized just how tall Pitch was. He himself wasn't short, but it seemed Pitch was a foot taller than him.

Jack swallowed, unsure why his throat was suddenly so dry.

"Tie me up?" he repeated, trying not to let his voice crack.

"Only if you're planning on running away, or . . ." Pitch said, hands trailing down Jack's arms as his voice dropped to a whisper, "you want me to."

Pitch's fingers wrapped around his wrists and brought them together, holding them there as a promise of what was to come. Jack stared at Pitch's long fingers encircling his wrists, all the way around and then some. Were they always able to do that? Jack swallowed again.

"I-if _you_ want to . . ."

"Jack, when it comes to what I want to do to you, the answer is always yes, no matter the question is. That's why I'm asking _you_."


	8. Bondage

This is a lot longer than planned. Oops. This may also be the last part for a while. Probably about two weeks. I apologize, but it's finals next week and then the week after is my last week in Japan and I want to make the most of it.

* * *

"Yes," Jack said, surprised at his own lack of hesitation. It just sounded so appealing. He wouldn't trust anyone other than Pitch to do this and it was something he very much wanted to try. Letting someone take over completely, so he didn't have to worry about anything . . . that sounded _very_ nice.

"Excellent."

Pitch pulled him out of the alley and released one of his wrists, though he kept a firm grip on the other. Jack didn't even mind this time. He rather liked not even having to think about where to go.

They went back to the same hotel from the other day, to the third floor this time. The door was a ways down the hall and Pitch still hadn't let go. He didn't until they were in the room with the door closed firmly behind them. Jack waited while Pitch pulled a length of rope from his bag, vaguely wondering if Pitch usually carried around all manner of sex toys or only what he wanted to do with him that day.

"I can do this several ways, depending on what you want, but all of them require you to be naked," Pitch said, gesturing for Jack to take his clothes off. As Jack did, Pitch continued talking, "I do want to warn you that once you are secured in the rope it will take a while to free you. The knots are complicated and difficult to undo, so you must tell me as soon as you being to feel uncomfortable."

Jack nodded as he placed his clothes to the side. He had some slight doubts about this now. His knowledge on this subject was nonexistent and Pitch's words did little to reassure him. Still, Pitch wouldn't do anything to hurt him and he needed to keep that in mind.

"Okay," he said, taking a deep calming breath.

"So, how would you like me to do this?" Pitch asked, walking around Jack, trailing the rope along his skin as he went. "I can restrain just your arms or tie your wrists to your legs or maybe even secure you to the bed so you really can't get away."

Jack shivered from the combination of the silky feel of rope and Pitch's words. "Whatever you wan—"

"No, no, Jack. How many times must I say it? This is about _you_."

"I-I don't know much about this . . ."

"That's okay. Just think about how you would be comfortable."

He would be comfortable if Pitch chose for him! He didn't mind servicing Pitch because he didn't have to worry about anything. Now Pitch was making him decide and what if he picked the wrong thing and Pitch didn't like it, so he never came back for Jack again. He couldn't afford that!

"I want whatever you want," he finally managed.

Pitch signed and looked somewhat disappointed.

"Very well then," he said. "I could keep going and say that what _I_ want is what _you_ want, but I believe you are just as stubborn as I am. Let's go with this for now . . ."

Pitch moved Jack's arms so they were behind his back, with his palms facing out so the backs of his hands pressed together. The rope looped around his wrists and up his arms, crisscrossing over his back and then wrapping around his chest. Jack felt himself getting hard throughout this process and he couldn't deny how much he liked not even having to worry about moving his body.

"Beautiful," Pitch said as he tied the final knot and ran his hands down Jack's rope-covered arms. "The black rope looks so lovely on you . . ."

Pitch walked into his line of sight, wearing an expression Jack had never seen before. It was something akin to wonder and amazement, but twisted with lust.

Pitch hooked a finger through a loop in the rope and tugged him toward the bed. He lay down on it himself first and then pulled Jack up so he was straddling his lap. Jack was glad for the steadying hand Pitch kept on his hips, not because he couldn't balance, but because he needed direction. Pitch's other hand reached around to spread lube on his hole and slip his fingers inside to stretch him.

As he did, Pitch kept up an endless litany of words. "You look gorgeous like this, you know that, Jack?" So willing and eager and all for me, only for me. But you still seem tense. There's no need for that. You can relax. Let me help you with that . . ."

Jack gasped as Pitch curled his fingers to hit his prostate. He relaxed his muscles and settled against the ropes. They tightened and pulled a bit in some areas, but overall kept him contained. It was much more comfortable like this and Jack let out a soft moan of contentment.

"There you go, Jack, that's it. Just like that . . . perfect."

Underneath him, Jack could feel how hard Pitch was. Pitch would want to enter him soon, most likely having Jack ride him, but Jack wasn't sure if he could do that. It put too much responsibility in his tied hands and giving him more control would just cause problems.

"You're tensing again," Pitch said. "I've got you, Jack. Don't worry."

Jack latched onto Pitch's words. He was telling him not to worry, so there was nothing to worry about. On his next breath out, Jack tried to relax again, focusing on one muscle at a time. Pitch's hand tightened on his hip and Jack melted into his grasp.

Humming in approval, Pitch removed his fingers from inside Jack and urged him to kneel up. Jack watched as Pitch up a condom on, still doubting his ability, but too afraid to voice it. Both of Pitch's hands found his hips again and guided Jack over his cock. The hands slipped around to pull his cheeks apart to expose his hole. Pitch's cock rested against it, slowly rubbing in circles as Pitch shifted his hips.

"Are you ready, Jack?"

Jack nodded, worked up from Pitch's motions. He whimpered as the head of Pitch's cock pushed into him. Pitch rocked up into him slowly, only the first few inches inside him at any point.

"Do you want more, Jack?" Pitch asked, but he continued talking before Jack could even nod his head in agreement. "Of course you do. Just look at you! I wish you could see yourself right now. The rope is so beautiful on you, with your pale skin, but it's not only the contrast. You just look lovely tied up. It's like you were _made_ for it."

Those words jolted Jack out of his sphere of pleasure. He wasn't _born_ for this; he was _made_, like an object, because that's what he was to Pitch and everyone else. He may like to pretend Pitch was different, that he _cared_, but it only made moments like this all the more painful.

There was really only himself to blame, for opening himself up in ways not required for a prostitute.

Even so, he nodded his head in agreement, because it was never about him and his feelings. It was always about the clients, what they want and what will keep them happy. And he especially needed to keep Pitch happy, not because he wanted to give him pleasure, but because he was a high-paying client.

"If you really want more, you'll have to get it yourself," Pitch said. "Ride me."

Jack was still unsure about having this much control, but it's what Pitch wanted, so he pressed himself down fully onto Pitch's cock. The way it filled him really did feel good and Jack instinctively tried to bring his hands up to stifle the whimpers spilling from his mouth, but his arms only twitched uselessly against the ropes.

"Good, you're almost there . . ." Pitch said. He kept one hand on Jack's hip to guide him down and slid the other up over his stomach and chest to twist his fingers over Jack's nipple. Jack gasped sharply and reflexively jerked his hips down. Strangely, he felt more secure with Pitch fully inside him. It was anchoring, in a way, and Pitch would soon begin talking again, reassuring Jack he was enjoying himself. Sure enough . . .

"Perfect, Jack, perfect. Up now, that's it. Don't worry, I've got you."

Jack simply followed Pitch's directions, letting him do as he wanted. It was so much nicer and easier that way.

"Just like that, Jack. Good, you're so good . . . let me hear you now."

Pitch's words of praise helped him further relax and Jack finally let out the moan he had been holding back in his throat. His bound arms made him feel less embarrassed, somehow, as if being unable to use his hands to quiet himself excused his noises.

Despite his lingering anxiety, this did feel good. Pitch's hand on his hip gave him direction and his other gave him distraction as it wrapped around his cock. The pace Pitch set wasn't too brutal and Jack was able to keep up with it. His legs would still most likely be sore the next day, since this wasn't a position often requested of him. Even his arms would hurt because of their position pulled behind his back, but he didn't mind, as the ropes helped him relax and eased his worries.

Maybe he could ask if Pitch would be willing to do this again. He certainly looked as if he was enjoying himself, so it wouldn't be too difficult to convince him.

Jack's next whimper stuttered into a moan as Pitch's cock brushed against his prostate. The next time he lowered himself down, Jack angled himself so Pitch would hit that spot again.

"There you go," Pitch encouraged, rolling his hips up to meet Jack. "Feels good, doesn't it? I wish I could make you feel like this all the time."

Jack whined as Pitch's thump swiped over the head of his cock. He tried not to get carried away by thoughts of feeling like this all the time. Sure, it felt good, but sexual pleasure wasn't the only thing he wanted to feel. He could recognize that, even being as caught up in it as he was. He couldn't imagine Pitch actually wanting that either. There had to be more to his life than coming to see Jack. Mentions of other responsibilities led him to believe so, but Pitch did come to see him nearly every day Jack was working the streets. Jack wondered what he did for money that gave him so much of it, yet also left him with that much free time.

A rough thrust against his prostate drew him out of those thoughts and reminded him he wanted to pay attention to what was going on. Pitch shifted below him, finding better leverage to thrust up into him. Jack wanted to speed up or increase the power of his downward slide, but he was too worried about falling or losing control, especially with Pitch so distracted. Not to mention himself.

Pitch was thrusting deeper into him and his hand was moving faster on his cock. Jack's arms strained against the ropes that bound them, but it made him feel secure and contained, safe even. It made it easy to get completely lost in the pleasure. Jack gave into it and let out the moans he had been holding back.

"Yessss, Jack that's it. That's exactly what I've been waiting for. It feels so good to let go, doesn't it? Just let me take care of you."

Too far gone, Jack could do nothing but frantically nod his head and even that small action took his concentration away from riding Pitch. He lost his rhythm, though not his balance, but it felt just as devastating. Pitch guided him back into it and made no comment, complaint or otherwise.

Jack opened eyes he didn't remember closing and looked down at Pitch to judge his expression. Pitch was looking up at him with only lust in his eyes, no sign of disappointment at Jack's faltering to be found. As he noticed Jack was watching, he smirked and moved his hand faster. Jack found himself slipping back into incoherency and willingly allowed himself to this time.

He dropped his head back and found himself moving faster. Pitch was babbling in the background, but Jack couldn't concentrate enough to listen. He was _so close_, hovering just on that glorious edge of simply feeling good and ultimate pleasure.

With one last hit to his prostate, he tripped over that edge, screaming as he came. He didn't care if the other guests in the hotel heard or about what Pitch would think. That was the best orgasm he had ever had. He'd felt contained and secured by the ropes, so much so that he was able to give himself over to the pleasure completely.

While he trembled from aftershocks, Pitch thrust up one final time before coming. Pitch's hands ran along his sides, slowly traveling up to his chest. His fingers caught on the ropes as they skimmed up to Jack's shoulders and then down his arms.

"Do you want me to untie you now?" Pitch asked.

Jack looked down at him and Pitch's expression said he very well knew what Jack's answer was going to be. ". . . not yet."

Pitch smirked and moved his hands to Jack's hips, encouraging him to kneel up and off his cock. Jack lay down on his side, mindful of his still-bound arms. It wasn't exactly comfortable, especially when Pitch got up to take care of the condom. Even though he still felt contained, Jack couldn't help but feel nervous without Pitch there beside him.

He came back quickly enough, with a warm towel to clean Jack off. His fingers trailed over the ropes once last time before lying down next to Jack.

"Are you feeling okay?" Pitch asked as he took him into his arms.

"Yeah, just . . . overwhelmed." Jack wasn't exactly sure how he felt. He certainly felt he was thinking more clearly now and was starting to regret a lot of his earlier behavior. That was definitely no way to act around a client.

"Take as much time as you need," Pitch said, a hand going to Jack's hair, stroking through tangled strands and rubbing calming circles onto his scalp.

Jack let the sensations soothe him, but they didn't stop the bubble of anxiety forming in his stomach. There was no denying that he very much enjoyed what just happened, but that was exactly what worried him. Sure, he typically liked what Pitch did to him, but he had never considered it as something he would like in his own personal sex life.

And his thoughts of his own personal sex life had never included Pitch before. He had actually thought of asking Pitch if they could do this again as if they were just some kinky couple! There was no "they" in their decision about the sex they had. Pitch was the client and, as such, he was in charge of that.

Also, Jack should not be cuddling with a client, with someone he had made _business transaction_.

Jack sat up quickly, jerking himself out of Pitch's arms. Startled, Pitch sat up as well.

"What's wrong? Are you sure you're okay?" Pitch's hand reached for his face, but Jack leaned back.

"Untie me." He kept his tone short and clipped, attempting to reestablish the distance that should be between them.

At Pitch's direction, Jack turned around, presenting his back to him. Deft fingers found and undid the knot and unwound the rope from his body. Once it had fallen completely away, Jack regretted his decision. His entire world came undone. There was no order in his flailing limbs, no safety in being set free. He found himself shaking and on the verge of sobbing and he couldn't stop it.

"Jack, you're most definitely not okay."

Pitch, Pitch was familiar and maybe not safe, but he was control and order and Jack needed that. He turned back toward Pitch and latched his hands onto the front of his shirt, burying his face in his chest. Pitch's arms were immediately around him, holding him tightly, almost as tightly as the ropes and that helped.

"It's okay, Jack, I've still got you."

Matching their breathing, Jack let himself be calmed by Pitch's words. He didn't know why he reacted so badly to that, but he was glad Pitch was there. Maybe that was inappropriate to need and think about a client like this, but if Pitch clearly wanted this as well then maybe it was okay. He was still doing what the client wanted and refusing wouldn't be good.

His own personal enjoyment from this may be because of a slight attraction to Pitch, but did that only exist because he associated Pitch with his money? If things were different, Jack wouldn't mind being this close to Pitch and feeling these things he felt for him. He would probably like it and endeavor to be even closer! And he wouldn't have to find excuses for liking it and things to justify it. Yet, if things had been different they wouldn't have met. Different meant he wasn't forced into selling his body on the streets, which was how they met in the first place.

Whatever he thought, things were the way they were and he could only work with what he had. Which wasn't much, but Jack had learned to make-do.

Tentatively, he put his arms around Pitch in return. Pitch stiffened in surprise, but quickly recovered and pulled Jack closer.

"Are you feeling better?" he asked, his lips brushing against Jack's bangs.

"Yea, a bit."

"Can you stay?"

Jack had his usual response ready, but he caught himself before spilling it. He really thought about it, long and hard. He definitely wanted to stay, but he truly couldn't. He needed to get Emma and take care of her. He promised they would go to the hospital tomorrow to visit their parents and he couldn't let her down.

"Not for too much longer," he finally answered.

"Then I'll cherish this while I can." Pitch pressed a kiss to the top of Jack's head, making him rethink all his previous convictions.

He was still unsure what to do, but he liked this. It was nice and he was warm and he didn't want to leave, but he couldn't stay with Pitch here forever. He let himself stay a little while longer, for now.

But there was still Emma to consider and it felt like too short of a time before he was saying, "I need to go now."

"So soon?" Pitch asked, though he let Jack detach himself and scoot back on the bed.

"Sorry—"

"No need to apologize." Pitch moved to the edge of the bed and took the envelope from the table.

Jack reached out to take it, but Pitch grabbed his wrist to pull him in. His other hand slipped around the side of his neck to steady his head and guide Jack's mouth to his. This kiss was must more heated then their last and only kiss. Pitch's tongue licked into his mouth and slid against his own, though he didn't coax him into reciprocation. Jack would like to, but he had no idea what to do and then it was over before he could think about taking action.

"Here you go," Pitch whispered, pressing the envelope into Jack's hand.

It took him a minute to recover, but he gripped the envelope and slid off the bed. He put his clothes on almost gingerly, aware of Pitch's eyes on him the entire time. When he was finished, he felt a bit awkward just heading straight for the door. He felt he should say or do something, but he couldn't fathom what.

Pitch saved him the effort by saying, "I'll see you Friday."

"Yeah." That was still a lame response, but it would have to do. Jack slipped out the door, not even bother with the elevators and going straight for the stairwell. He thundered down the stairs, almost tripping on the unfamiliar flight, but once he was outside he could breathe and think again. Maybe his logic was a bit faulty and heavily influenced by his need for money, but he deserved to be happy, didn't he?

Even if he was fooling himself?

At this point Jack was willing to take what he could get. This may be just a facsimile of happiness and a farce of a relationship—even if it was based on money—it still existed. There was not much he could do but accept it. As long as it was what Pitch wanted, right?


End file.
